Tocopherol side chain synthesis via asymmetric organocatalytic transfer hydrogenation and convenient measurement of stereoselectivity

Title
Tocopherol side chain synthesis via asymmetric organocatalytic transfer hydrogenation and convenient measurement of stereoselectivity
Author(s)
정병선이현지이채민김동국손미선남태규[남태규]
Keywords
BREAKING PHENOLIC ANTIOXIDANTS; VITAMIN-E; ALPHA-TOCOPHEROL; AMINOPYRIDINOL ANTIOXIDANTS; ENANTIOSELECTIVE SYNTHESIS; BIOLOGICAL MOLECULES; LIPID-PEROXIDATION; HANTZSCH ESTERS; DERIVATIVES; RADICALS
Issue Date
201410
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Citation
TETRAHEDRON LETTERS, v.55, no.43, pp.5895 - 5897
Abstract
An asymmetric synthetic route for 1-iodofarnesane, a key intermediate for tocopherol side chain synthesis, starting from (+)-(R)-citronellal was developed. 1-Iodofamesane was prepared through eight steps in about 50% overall yield, and asymmetric transfer hydrogenation of the enal with a chiral organocatalyst was conducted as a stereoinduction step. To measure the stereoinduction level and optical purity of the product, a convenient analytical method was developed in which a phenylcarbamate derivative of the C-15 alcohol was found to be suitable to give proper polarity and UV-activity for chiral UV-HPLC analysis. (C) 2014 Elsevier Ltd. All rights reserved.
URI
http://hdl.handle.net/YU.REPOSITORY/30698http://dx.doi.org/10.1016/j.tetlet.2014.08.085
ISSN
0040-4039
Appears in Collections:
약학대학 > 약학부 > Articles
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